Chemoselective synthesis of dithymidine phosphorothioate in solution using O-protected thiophosphate monomers

被引：1

作者：

Boesen, T ^{[1
]}

Kehler, J ^{[1
]}

Dahl, O ^{[1
]}

机构：

[1] Univ Copenhagen, HC Orsted Inst, Dept Chem, DK-2100 Copenhagen, Denmark

来源：

NUCLEOSIDES & NUCLEOTIDES | 1999年 / 18卷 / 6-7期

关键词：

D O I：

10.1080/07328319908044676

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Diastereomerically pure O-protected thymine monothioate nucleotide (I) is efficiently coupled to protected thymidine (II) in a chemoselective, but not stereoselective manner, to give dithymidine phosphorothioates (III).

引用

页码：1241 / 1242

页数：2

共 10 条

[1] Solid phase synthesis of oligodeoxynucleoside phosphorodithioates by a phosphotriester method using a chemoselective coupling reagent [J].

Kehler, J ;

Puschl, A ;

Dahl, O .

TETRAHEDRON LETTERS, 1996, 37 (44) :8041-8044

[2] SYNTHESIS OF S-ALKYL ESTERS OF PROTECTED 2'-DEOXYRIBONUCLEOSIDE 3'-PHOSPHOROTHIOATES - BUILDING-BLOCKS FOR THE LARGE-SCALE SYNTHESIS OF PHOSPHOROTHIOATE ANALOGS OF OLIGODEOXYRIBONUCLEOTIDES BY THE PHOSPHOTRIESTER APPROACH IN SOLUTION [J].

LIU, XH ;

REESE, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (13) :1685-1694

[3]

MILLER B, 1962, P CHEM SOC LONDON, P303

[4] Solution phase synthesis of dithymidine phosphorothioate by a phosphotriester method using new S-protecting groups [J].

Puschl, A ;

Kehler, J ;

Dahl, O .

NUCLEOSIDES & NUCLEOTIDES, 1997, 16 (1-2) :145-158

[5] CHEMICAL SYNTHESIS OF OLIGO-NUCLEOTIDES AND POLY-NUCLEOTIDES BY PHOSPHOTRIESTER APPROACH [J].

REESE, CB .

TETRAHEDRON, 1978, 34 (21) :3143-3179

[6] A new approach to the synthesis of oligonucleotides and their phosphorothioate analogues in solution [J].

Reese, CB ;

Song, QL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (21) :2787-2792

[7] Preparation of an octadeoxyribonucleoside heptaphosphorothioate by the phosphotriester approach in solution [J].

Reese, CB ;

Song, QL ;

Rao, MV ;

Beckett, I .

NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (1-3) :451-470

[8] DIASTEREOMERS OF NUCLEOSIDE 3'-O-(2-THIO-1,3,2-OXATHIA(SELENA)PHOSPHOLANES) - BUILDING-BLOCKS FOR STEREOCONTROLLED SYNTHESIS OF OLIGO(NUCLEOSIDE PHOSPHOROTHIOATE)S [J].

STEC, WJ ;

GRAJKOWSKI, A ;

KOBYLANSKA, A ;

KARWOWSKI, B ;

KOZIOLKIEWICZ, M ;

MISIURA, K ;

OKRUSZEK, A ;

WILK, A ;

GUGA, P ;

BOCZKOWSKA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (49) :12019-12029

[9] NOVEL ROUTE TO OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES) - STEREOCONTROLLED SYNTHESIS OF P-CHIRAL OLIGO(DEOXYRIBONUCLEOSIDE PHOSPHOROTHIOATES) [J].

STEC, WJ ;

GRAJKOWSKI, A ;

KOZIOLKIEWICZ, M ;

UZNANSKI, B .

NUCLEIC ACIDS RESEARCH, 1991, 19 (21) :5883-5888

[10] Stereocontrolled synthesis of dithymidine phosphorothioates by use of a functionalized 5′-protecting group bearing an imidazole residue [J].

Wada, T ;

Kobayashi, N ;

Mori, T ;

Sekine, M .

NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (1-3) :351-364

← 1 →